In February, 2010, the International Herald Tribune published an article by then columnist Philip Bowring about Asian political dynasties, in which he included Singapore. A month later The New York Times, which owns the IHT, published a very bizarre apology:

In 1994, Philip Bowring, a contributor to the International Herald Tribune’s op-ed page, agreed as part of an undertaking with the leaders of the government of Singapore that he would not say or imply that Prime Minister Lee Hsien Loong had attained his position through nepotism practiced by his father Lee Kuan Yew. In a February 15, 2010, article, Mr. Bowring nonetheless included these two men in a list of Asian political dynasties, which may have been understood by readers to infer that the younger Mr. Lee did not achieve his position through merit. We wish to state clearly that this inference was not intended. We apologize to Prime Minister Lee Hsien Loong, Minister Mentor Lee Kuan Yew and former Prime Minister Goh Chok Tong for any distress or embarrassment caused by any breach of the undertaking and the article.

In 1994 lawyers representing Singapore’s leaders had taken the newspaper to court for the article mentioned above and another one (which, ironically, suggested that some Asian leaders relied “on a compliant judiciary to bankrupt opposition politicians” without even mentioning Singapore.) The IHT apologized, settled the $678,000 in libel damages, and, as part of the settlement Bowring agreed that he would not say or imply that Lee Hsien Long took office through nepotism. (Singapore has been ruled by Lee Hsien Long since 2004; his father Lee Kuan Yew ruled as prime minister from 1959-1990 and then behind the scenes after that.) Singapore courts found the newspaper and Bowring guilty of libel in 2010–because they broke the terms of their 1994 agreement to refrain from alleging that Singapore’s leaders engaged in nepotism–and the newspaper paid $114,000 in damages and costs.

Singapore, a city-state of 5 million people armed with some of the world’s strongest libel laws, successfully coerced the world’s most prestigious newspaper into retracting coverage that was only mildly critical.

Fast forward to Thursday October 25, when The New York Timespublished a damning investigation into the family of China’s Premier Wen Jiabao, uncovering that his family has controlled assets worth at least $2.7 billion. It was the third story published by Western media this year (Bloomberg published the other two) that discovered great, possibly ill-gotten wealth in the families of high-ranking Chinese officials. On Friday, China’s foreign ministry spokesman Hong Lei said the article “smears China and has ulterior motives.”

The website of the official newspaper of the Communist Party, the People’s Web, published a poorly crafted critique of the New York Times. The website of the New York Times English and Chinese language site was blocked, and the New York Times business in China is likely to suffer. Up until this point, China’s reaction to the article had been standard and, besides some lost traffic from the blocking, ineffective; smoke and no fire.

But worringly, on Sunday, two lawyers representing Wen’s family issued a statement in a Hong Kong newspaper claiming that “the so-called ‘hidden riches’ of Wen Jiabao’s family members in the New York Times’ report does not exist,” and adding that “we will continue to make clarifications regarding untrue reports by the New York Times, and reserve the right to hold it legally responsible.”

What if Wen and his family decide to take the New York Times to court and sue it for defaming Wen Jiabao or the Communist Party? Sure, Wen and his family would likely prefer the embarassing story to fade away, especially as it’s just weeks away from the 18th Party Congress, where Wen and his peers are expected to formally begin to yield power to the next generation of Chinese leadership. And because China has a far worse reputation for cracking down on press freedom than Singapore does, one can expect the Times to fight much harder this time. But this is a case that Wen and his family could surely win in a Chinese court.

Back in April 2010 the then New York Times public editor Clark Hoyt wrote an article addressing the Singapore apology. He explained the outsized importance of Singapore as a market for English-language media, expressed how Singapore’s leaders had never lost a libel suit in their own courts, and quoted Stuart Karle, a former general counsel of the Wall Street Journal, saying, “If you want to be a global paper, it has lots of banks, lots of commerce, a highly educated, English-speaking population…It’s hard to turn your back on that.

Hoyt added: “For The Herald Tribune and all the other news organizations that have paid damages to Singapore’s rulers (The Wall Street Journal, The Economist, Bloomberg) or had their circulation limited there (Time, The Asian Wall Street Journal, The Economist), the choice has been to stay.”

Singapore’s successful authoritarianism has long been seen as a model for China. China’s market is also much larger than Singapore’s. For the sake of press freedom, here’s hoping that the Times is not forced to apologize to China.